For your car, make sure the car is ready to be imported (so is modified up to Canadian safety standards, is owned outright so no loan on it, etc etc). I think at some border crossings you should make an appointment to import the car (there is lots of info online or on this forum on the topic). You will need to pay all taxes, fees, duties etc depending what province it's being imported to and where the car was made.
Note that if you're reported for not meeting the RO, there's a chance you'll have your PR status revoked in the next few years and asked to leave Canada, so would then need to import it back from Canada to USA.
And as mentioned, if you do get into Canada without being reported, you must then stay here 2 straight years without leaving even once for any reason, to come back into compliance with the RO. During these 2 years you can't sponsor your wife and kid, so they must continually apply to extend their visitor status and hope it's accepted. Your wife will be unable to work all this time (unless she can get a work permit independently). Heatlhcare coverage will depend on province, but in most provinces visitors are not covered so if this is the case you need 2+ years of travel medical insurance for them and they wouldn't be covered for routine things like checkups, vaccinations, etc etc.